120128-20-3

Basic information

• Product Name: 5-[2-[4-(Quinolin-2-ylmethoxy)phenoxymethyl]benzyl]-1H-tetrazole
• Synonyms: RG-12525; 2-[(4-{[2-(2H-tetrazol-5-ylmethyl)benzyl]oxy}phenoxy)methyl]quinoline
• CAS NO: 120128-20-3
• Molecular Formula: C₂₅H₂₁N₅O₂
• Molecular Weight: 423.4665
• Mol File: 120128-20-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 667°C at 760 mmHg
• Flash Point: 227.3°C
• Density: 1.308g/cm³
• Vapor Pressure: 1.17E-17mmHg at 25°C
• Refractive Index: 1.681
• CAS DataBase Reference: 5-[2-[4-(Quinolin-2-ylmethoxy)phenoxymethyl]benzyl]-1H-tetrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[2-[4-(Quinolin-2-ylmethoxy)phenoxymethyl]benzyl]-1H-tetrazole(120128-20-3)
• EPA Substance Registry System: 5-[2-[4-(Quinolin-2-ylmethoxy)phenoxymethyl]benzyl]-1H-tetrazole(120128-20-3)

Safety Data

• Hazardous Substances Data: 120128-20-3(Hazardous Substances Data)

Upstream product

• 3747-74-8 2-(chloromethyl)quinoline monohydrochloride 
• 91-63-4 2-methylquinoline 
• 612-12-4 o-Xylylene dichloride 
• 188255-02-9 5-(2-Bromomethyl-benzyl)-1H-tetrazole 
• 188255-00-7 [2-(1H-Tetrazol-5-ylmethyl)-phenyl]-methanol 
• 123-31-9 hydroquinone 
• 6627-91-4 2-cyanomethylbenzoic acid 
• 124993-40-4 2-[(4-hydroxyphenoxy)methyl]quinoline 
• 19820-77-0 quinolin-2-ylmethyl 4-methylbenzenesulfonate 
• 188255-05-2 2-{4-[2-(2-Trityl-2H-tetrazol-5-ylmethyl)-benzyloxy]-phenoxymethyl}-quinoline 
• 188255-07-4 2-(4-{2-[1-(Tetrahydro-pyran-2-yl)-1H-tetrazol-5-ylmethyl]-benzyloxy}-phenoxymethyl)-quinoline 
• 124993-49-3 2-<<4-(2-quinolinylmethoxy)phenoxy>methyl>benzyl cyanide 
• 124993-48-2 2-<<4-(2-quinolinylmethoxy)phenoxy>methyl>benzyl chloride 
• 188255-03-0 5-(2-Bromomethyl-benzyl)-2-trityl-2H-tetrazole 

Relevant articles and documents

The process development of RG 12525 (2-{[4-(Tetrazol-5-ylmethylphenyl)-methoxy]phenoxymethyl}quinoline)

This contribution describes process improvements to provide a practical and cost-effective synthesis for the manufacture of RG 12525 which resulted in a 3-fold increase in overall yield. Improved solvent systems for chlorination and azidation reactions are described. Adjustments to the tetrazole-forming step eliminated azide sublimation and minimised this risk on scale-up. A robust solvent system was found to control the polymorphic form during crystallisation, which had hitherto been difficult due to the near-equivalence of melting points (154 and 157 °C) of the two known forms.

Therapeutic uses of quinoline derivatives

A method for mediating the activity of PPAR-γ receptor comprising contacting said PPAR-γ receptor with a compound of formula I defined herein. Also disclosed is the treatment of a patient suffering from a physiological disorder capable of being modulated

A convergent synthesis of an LTD4 antagonist, RG12525

An efficient, convergent synthesis of an LTD4 antagonist, RG12525 (1) has been achieved through the alkylation of the (2-quinolinylmethoxy)phenol (2) with either a triphenylmethyl protected tetrazole synthon (4a) or with a tetrahydropyranyl derivative (4b). Preparation of synthons 4a and 4b, as well as novel preparation of 2 is described.